benzyl-4,6-di-O-benzoyl-2-deoxy-α-D-erythro-hexopyranoside-3-ulose | 1204193-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl-4,6-di-O-benzoyl-2-deoxy-α-D-erythro-hexopyranoside-3-ulose
• 英文别名: [(2R,3R,6S)-3-benzoyloxy-4-oxo-6-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 1204193-30-5
• 化学式: C₂₇H₂₄O₇
• 分子量: 460.483
• InChiKey: XWJWJAXKPQVPKN-DSITVLBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,6-di-O-benzoyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose 、 苯甲醇 在 aluminum (III) chloride 作用下， 以90%的产率得到benzyl-4,6-di-O-benzoyl-2-deoxy-α-D-erythro-hexopyranoside-3-ulose
  参考文献：
  名称：

  Microwave-assisted stereoselective α-2-deoxyglycosylation of hex-1-en-3-uloses

  摘要：

  alpha-2-Deoxyglycosides were successfully synthesized by means of microwave-assisted glycosylation. Hex-1-en-3-uloses were treated with a catalytic amount of AlCl3 and various O-nucleophiles including alcohols and sugars under microwave conditions. The desired alpha-2-deoxy-ulosides products were obtained in good to excellent yields with high stereoselectivity (alpha/beta >= 88/12). Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.049

文献信息

• Microwave-assisted stereoselective α-2-deoxyglycosylation of hex-1-en-3-uloses
  作者：Hui-Chang Lin、Hsu-Hsuan Wu、Zi-Ping Lin、Chih-Yuan Lin、Chun-Hung Lin、Kun-Lung Chen、Fung Fuh Wong

  DOI：10.1016/j.tetlet.2009.10.049

  日期：2009.12

  alpha-2-Deoxyglycosides were successfully synthesized by means of microwave-assisted glycosylation. Hex-1-en-3-uloses were treated with a catalytic amount of AlCl3 and various O-nucleophiles including alcohols and sugars under microwave conditions. The desired alpha-2-deoxy-ulosides products were obtained in good to excellent yields with high stereoselectivity (alpha/beta >= 88/12). Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.